N¹-(4-chloro-2-nitrophenyl)-N²,N²-dimethylethane-1,2-diamine | 4926-56-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N¹-(4-chloro-2-nitrophenyl)-N²,N²-dimethylethane-1,2-diamine
• 英文别名: N-(2-Dimethylamino-ethyl)-4-chlor-2-nitro-anilin；N'-(4-chloro-2-nitrophenyl)-N,N-dimethylethane-1,2-diamine；N-(4-chloro-2-nitrophenyl)-N',N'-dimethylethane-1,2-diamine
• CAS: 4926-56-1
• 化学式: C₁₀H₁₄ClN₃O₂
• mdl: MFCD00631296
• 分子量: 243.693
• InChiKey: BJQJYGBOWKQYTR-UHFFFAOYSA-N

物化性质

• 沸点：
  376.3±37.0 °C(Predicted)
• 密度：
  1.286±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N¹-(4-chloro-2-nitrophenyl)-N²,N²-dimethylethane-1,2-diamine 在 盐酸 、 tin(ll) chloride 作用下， 以 xylene 为溶剂， 反应 20.5h， 生成 1,2,3,3a-tetrahydro-9-(2-dimethylaminoethyl)-6-chlorocyclopenta<1,5>benzodiazepin-10(9H)-one
  参考文献：
  名称：

  Mule; Pirisino; Moretti, Bollettino Chimico Farmaceutico, 1994, vol. 133, # 3, p. 167 - 172

  摘要：

  DOI：
• 作为产物：
  描述：

  N,N-二乙基乙二胺 、 2,5-二氯硝基苯 以 N,N-二甲基甲酰胺 为溶剂， 生成 N¹-(4-chloro-2-nitrophenyl)-N²,N²-dimethylethane-1,2-diamine
  参考文献：
  名称：

  Synthesis and Anti-inflammatory Evaluation of Novel Benzimidazole and Imidazopyridine Derivatives

  摘要：

  Sepsis, an acute inflammatory disease, remains the most common cause of death in intensive care units. A series of benzimidazole and imidazopyridine derivatives were synthesized and screened for anti-inflammatory activities, and the imidazopyridine series showed excellent inhibition of the expression of inflammatory cytokines in LPS-stimulated macrophages. Compounds X10, X12, X13, X14, and X15 inhibited TNF-alpha and IL-6 release in a dose-dependent manner, and X12 showed no cytotoxicity in hepatic cells. Furthermore, X12 exhibited a significant protection against LPS-induced septic death in mouse models. Together, these data present a series of new imidazopyridines with potential therapeutic effects in acute inflammatory diseases.

  DOI：

  10.1021/ml300282t

文献信息

• Riminophenazine Derivatives as Potential Antituberculosis Agents: Synthesis, Biological, and Electrochemical Evaluations
  作者：Mpelegeng Victoria Bvumbi、Chris van der Westhuyzen、Edwin M. Mmutlane、Andile Ngwane

  DOI：10.3390/molecules26144200

  日期：——

  have been designed and synthesized. Preliminary investigations into the relationship between lipophilicity, redox potential, and antimycobacterial activity were conducted, using the in vitro activity against Mycobacterium tuberculosis H37Rv, mammalian cytotoxicity, and the redox potential of the compounds determined by cyclic voltammetry as measures. Results revealed an activity “cliff” associated with

  已经设计并合成了一系列新的 riminophenazine 衍生物，在 N-5 处具有可电离的烷基取代基，并在 C-3 亚氨基氮、C-8 处和侧基芳基上具有多种取代基。使用对结核分枝杆菌H 37 Rv 的体外活性、哺乳动物细胞毒性和循环伏安法测定的化合物的氧化还原电位作为措施，对亲脂性、氧化还原电位和抗分枝杆菌活性之间的关系进行了初步研究。结果显示与 C-8 替代相关的活动“悬崖”（10l和10m)，连同定义的氧化还原活性，指出一类新的 riminophenazines 作为具有合理活性 (MIC 99 ~1 µM) 的潜在抗结核剂。
• Savelli; Boido; Mule, Il Farmaco, 1989, vol. 44, # 2, p. 125 - 140
  作者：Savelli、Boido、Mule、Piu、Alamanni、Pirisino、Satta、Peana

  DOI：——

  日期：——
• SAVELLI, F.;BOIDO, A.;MULE, A.;PIU, L.;ALAMANNI, M. C.;PIRISINO, G.;SATTA+, FARMACO, 44,(1989) N, C. VAR PAG.
  作者：SAVELLI, F.、BOIDO, A.、MULE, A.、PIU, L.、ALAMANNI, M. C.、PIRISINO, G.、SATTA+

  DOI：——

  日期：——
• Mule; Pirisino; Moretti, Bollettino Chimico Farmaceutico, 1994, vol. 133, # 3, p. 167 - 172
  作者：Mule、Pirisino、Moretti、Savelli、Boido、Satta、Peana

  DOI：——

  日期：——
• Synthesis and Anti-inflammatory Evaluation of Novel Benzimidazole and Imidazopyridine Derivatives
  作者：Gaozhi Chen、Zhiguo Liu、Yali Zhang、Xiaoou Shan、Lili Jiang、Yunjie Zhao、Wenfei He、Zhiguo Feng、Shulin Yang、Guang Liang

  DOI：10.1021/ml300282t

  日期：2013.1.10

  Sepsis, an acute inflammatory disease, remains the most common cause of death in intensive care units. A series of benzimidazole and imidazopyridine derivatives were synthesized and screened for anti-inflammatory activities, and the imidazopyridine series showed excellent inhibition of the expression of inflammatory cytokines in LPS-stimulated macrophages. Compounds X10, X12, X13, X14, and X15 inhibited TNF-alpha and IL-6 release in a dose-dependent manner, and X12 showed no cytotoxicity in hepatic cells. Furthermore, X12 exhibited a significant protection against LPS-induced septic death in mouse models. Together, these data present a series of new imidazopyridines with potential therapeutic effects in acute inflammatory diseases.